Benzylamine → (3aR*,10aS*)-9-Benzyl-4-((benzylamino)acetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-one

HRID 356175Notes

Reaction equation

HRID 356175 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[N:11]([C:19](=[O:22])[CH2:20]Cl)[C:10]2[CH:23]=[CH:24][CH:25]=[CH:26][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[N:11]([C:19](=[O:22])[CH2:20][NH:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:10]2[CH:23]=[CH:24][CH:25]=[CH:26][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 70110192(3aR*,10aS*)-9-Benzyl-4-(chloroacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 70111495(3aR*,10aS*)-9-Benzyl-4-((benzylamino)acetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-oneYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3aR*,10aS*)-9-benzyl-4-(chloroacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one (1.0 g, 2.7 mmol) and benzylamine (1.45 g, 13.6 mmol) in ethanol (30 mL) was added potassium carbonate (560 mg, 4.1 mmol), and the mixture was refluxed for 17 hours. The solvent was distilled off. To the residue was added water, which was subjected to extraction with dichloromethane. The extract was washed with water, dried and, then, the solvent was distilled off. The residue was purified by silica-gel column chromatography (ethyl acetate-hexane 1:1), followed by crystallization from diethyl-ether to give 0.36 g (yield 30%), m.p. 95-98° C.

Workup

  1. temperaturethe mixture was refluxed for 17 hours
  2. distillationThe solvent was distilled off
  3. additionTo the residue was added water, which
  4. extractionwas subjected to extraction with dichloromethane
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by silica-gel column chromatography (ethyl acetate-hexane 1:1)
  9. customfollowed by crystallization from diethyl-ether
  10. customto give 0.36 g (yield 30%), m.p. 95-98° C.

Sources & evidence

ORD record
ord-c494e03ffa31465ca236f6b15f9a37b8
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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